Fan fiction and fever dreams with Mallory Ortberg

The prolific satirist shares what’s in store for subscribers to her new paid newsletter, The Shatner Chatner.

Writer Mallory Ortberg. Photo: Supplied

“I can’t promise you that every issue is going to explicitly be about William Shatner,” says Mallory Ortberg, discussing The Shatner Chatner. “But I can promise you that everything will be inexplicitly and hazily motivated by my shifting feelings for him.”

Ortberg amassed a devoted following while writing art and pop culture satire for The Toast – the feminist general interest website she co-founded with Nicole Cliffe. The profound nature of the site’s fandom is best described by the fact that one reader was able to find a living kidney donor through a relationship formed in the comments section.

The Toast disbanded a year-and-a-half ago, and Ortberg decided to start a newsletter because she missed having an outlet for comedy. “I’ve just been saving it all up,” explains Ortberg, who has been working on her upcoming book, The Merry Spinster, in the interim. “That’s not a state that I can find myself in for a long time before I start to explode like a volcano with dumb jokes.”

Ortberg enjoys writing for other outlets, but says the pitching process can be tiring. “I have to come up with a description of something I want, I have to come up with a place that I think would be interested and get approval from an editor and then go back and forth … Usually by that point I’m like, ‘ugh, it’s been three days since I had this idea. I’m bored!’” She likes the immediacy of self-publishing, where “from thought to action there’s no distance.”

The Shatner Chatner is hosted by Substack, a newsletter publishing start-up co-founded by San Francisco-based New Zealander Hamish McKenzie that allows writers to charge their subscribers. Before moving to Substack, Ortberg was publishing the newsletter on TinyLetter but had reached the subscriber limit. She contemplated swapping to MailChimp, but had hesitations about the publishing fee.

“I’d be like, ‘well, I used to make money at The Toast, and then I wrote a newsletter for free, and then I started paying to write a newsletter.’” Making money through Substack means she’ll be able to spend more time on The Shatner Chatner instead of feeling like she should be working on her book or pitching a new one. “Doing things for free is wonderful, but there’s only so much time I can devote to that kind of work,” she says.

The newsletter has four free issues per month, as well as an additional weekly issue for a monthly subscription payment of $US5. Ortberg also offers subsidised payment options for students and low-income readers. “I’m jazzed that there will be stuff available for anybody even if they can’t afford it. It’s not like it’s all going to be paywalled.”

Ortberg takes comfort in the directness of paid newsletters. “We’re living in very bewildering times,” she says, describing the instability of online writing. “I’m such a non-expert on what media models work and what don’t. I mean, I had a website for three years and now I don’t so my guess is as good as anybody else’s … I think what’s helpful about something like this is it’s pretty simple.”

For Ortberg, private newsletters also offer a safe haven from harassment. “I’ve been doing this for long enough now that it’s just sort of understood that you’re going to encounter some of that, and it sucks,” she says. “That’s not to say the real world is dark and terrible and here is a respite from that with some fake cheer … You just have to set limits for yourself. I definitely do not go out of my way to spend more time online that I have to, and I try to focus on the people and the projects that I’m really excited about.”

She believes that receiving newsletters can be beneficial for readers, too. “There’s something that can be meaningful, soothing, helpful about having something that is very specific, that’s not coming at you unexpectedly, that arrives in your inbox because you asked for it and you’re not encountering it by surprise and it’s not jarring – or if it is jarring you’re at least ready for it. I think that can be really lovely.”

Ortberg feels that the intimacy of the format also changes her tone. ”I feel more introspective, more gentle, less bombastic,” she says. “Which is not to say that it’s like Mallory unplugged. But actually, that’s a great way of putting it. Like, the jokes and the goofiness are still there, but there’s a little more sense of personal vulnerability – it’s more like sitting down one-on-one with somebody as opposed to giving a talk before a crowded room.”

Fans of The Toast will be pleased to hear that Ortberg is planning to revisit some of her favourite on-going series. “I want to do more and more sequels to things that I’ve been unable to stop thinking about,” she says. Subscribers can expect updates on her much loved Two Monks Inventing Things series, and she has already published a new instalment of People’s Sexiest Man Alive, a dystopian YA fan fiction series in which winners of the title ritualistically sacrifice one another.

Ortberg says there will also be plenty of entirely new content. “I don’t want to just make it The Toast round two,” she explains. In her first issue for Substack, she wrote a series of surreal plotlines for the ‘90s sitcom Frasier based on a recent fever dream she had. “I spend a lot of time thinking about Frasier,” she says. “That show is helping me figure out myself.”

She’s also excited to work with new mediums like video. Six months ago, she ordered a $12 wig – a severe silver bob – and started recording herself impersonating Joan Didion and Anna Wintour. “I just had this image of them like two elder gods addressing one another, unrestrained by mortal concerns,” she says.

“I’m definitely looking to expand the Anna and Joan universe and try to figure out what different formats I want to play with and what different types of writing I want to add to the site,” says Ortberg. “I’m pretty jazzed to see what I can do there…. I’m sure I will have some more dumb ideas. As soon as I start putting on wigs and doing stupid voices it’s just matter of time.”